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Novel PI Analogues Selectively Block Activation of the Pro-survival Serine/Threonine Kinase Akt
Abstract
The synthesis from l-quebrachitol of a series of 3-deoxygenated ether lipid-type phosphatidylinositol (PI) analogues is reported, that selectively block activation of Akt and downstream substrates without affecting activation of the upstream kinase, PDK-1, or other kinases downstream of ras such as MAPK in H157 and H1703 lung cancer cells that have high levels of constitutively active Akt. The 2-hydroxyl in these compounds was deleted or alkylated with the intent to preclude metabolic degradation of these compounds by PI-specific phospholipase C (PI-PLC). PI analogues with phosphate linkers are more effective than those with carbonate linkers. Specific inhibition of Akt by these compounds validates ligand design targeted to the PH domains of crucial signaling proteins, thus providing a unique class of possible cancer therapeutics.
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Cited by
Targeting the PI3K-Akt pathway in human cancer
Luo, J., Manning, B. D., & Cantley, L. C. (2003) · Cancer Cell · doi:10.1016/s1535-6108(03)00248-4 · Cited by 1,290
Jaworski, J., Spangler, S., Seeburg, D. P., Hoogenraad, C. C., & Sheng, M. (2005) · The Journal of Neuroscience · doi:10.1523/jneurosci.2270-05.2005 · Cited by 579
Allosteric Akt (PKB) inhibitors: discovery and SAR of isozyme selective inhibitors
Lindsley, C. W., Zhao, Z., Leister, W. H., Robinson, R. G., Barnett, S. F., Defeo-Jones, D., Jones, R. E., Hartman, G. D., Huff, J. R., Huber, H. E., et al. (2005) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2004.11.011 · Cited by 503
PI(3) kinase is associated with a mechanism of immunoresistance in breast and prostate cancer
Crane, C. A., Panner, A., Murray, J. C., Wilson, S. P., Xu, H., Chen, L., Simko, J. P., Waldman, F. M., Pieper, R. O., & Parsa, A. T. (2009) · Oncogene · doi:10.1038/onc.2008.384 · Cited by 181
Naito, A. T., Akazawa, H., Takano, H., Minamino, T., Nagai, T., Aburatani, H., & Komuro, I. (2005) · Circulation Research · doi:10.1161/01.res.0000175241.92285.f8 · Cited by 121
Metadata
- Authors
- Kozikowski, A. P., Sun, H., Brognard, J., & Dennis, P. A.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-01-08
- Volume
- 125
- Issue
- 5
- Pages
- 1144-1145
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1997611649
- Cited by
- 198
- References
- 0
- FWCI
- 9.97
- Type
- journal article
- Language
- en
- Open access
- closed
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- Kozikowski, A. P., Sun, H., Brognard, J., & Dennis, P. A. (2003). Novel PI Analogues Selectively Block Activation of the Pro-survival Serine/Threonine Kinase Akt. Journal of the American Chemical Society. https://doi.org/10.1021/ja0285159
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